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NameProf. Xiaodong Shi
EmailEmail hidden; Javascript is required.
OrganizationUniversity of South Florida
PositionFaculty
InvitedNo
TypeOral
TopicOrganic Chemistry
Title

Regioselective Crossed Aldol Reactions and Alkyne Trifunctionalization via Au-Fe Catalysis

Author(s)

Xiaodong Shi

Author Location(s)

University of South Florida

Abstract

Our report presents a novel gold-iron (Au-Fe) catalytic system for the alkyne hydration and vinyl Au addition to aldehydes or ketones, achieved through the simultaneous construction of C–C, C–O, and C–N bonds, with Fe(acac)3 as an essential co-catalyst. By utilizing a γ-keto directing group, sequential gold-catalyzed alkyne hydration, vinyl-gold nucleophilic addition, and gold(III) reductive elimination were achieved in one pot, resulting in alkyne trifunctionalization. Additionally, we report on the successful TA–Au catalyzed styryl dehydro-Diels–Alder reaction and the first example of constructing dihydropyridine in a formal [3+2+1] fashion using the gold-catalyzed intermolecular amine addition to diyne-ene, resulting in excellent yields and enantioselectivity.

Date06/02/2023
Time10:45 AM